Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
5+ acres, private pool, wide water, sandy beach, dock, boats, firepit & bikes Beautiful, newer custom 3-story home w/ wrap-around porches, 7 bedrooms & 5 baths & can accommodate up to 18 guests*. The 3rd floor is a haven for kids with a game room, two bdrms & a bath. Close to town, yet your own, secluded compound for extended family & friends. Gorgeous upscale neighborhood just 10 mins from Cambridge & Easton MD. A perfect retreat with massive entertaining areas.
Family retreat perfection! "Saddle Beach", our fabulous, newer waterfront owner’s home is on 500 feet of private Chesapeake waterfront. It’s a grand vacation home with idyllic wrap around porches, your own private pool, dock, beach and pond. It's just 10 minutes from the renowned Hyatt Chesapeake Bay Spa and Resort, countless restaurants and quaint shops and, if it suits you, less than an hour from Ocean beaches.
'Saddle Beach' is on Dorchester County's exclusive McKeil Point neighborhood on the Little Choptank river, just off the Chesapeake Bay. The property has a mile-wide view and a 200' dock. The home is exceptionally furnished, with 4200sf of living area with another 1200sf of open and screened porches. 6 bedrooms and a sleeper den with sofa-bed and bath with walk-in shower. A large eat-in kitchen, two full size refrigerators, massive open entertaining area with 3 living rooms and a study. The 3rd floor is designed for kids with a recreation area, wide dormers, a full bath, and two bedrooms with 8 beds. An in-ground pool is off the porch & the home has beautiful millwork and exotic, reclaimed hand-cut wide-plank walnut floors. A lovely tidal pond is just off the living room.
The Property: The perfect Family Retreat! Gorgeous wrap around porches include a screened outdoor eating area overlooking the pool. The compound was designed as an owners' dream, and includes a pool, ample decks for entertainment, a gorgeous beach, private natural setting, and walkways to the adjacent marsh. Towering pines, aromatic cedars, and marsh grasses dot the landscape. There is a rustic tidal pond next to the house providing rest for swans, ducks, & geese. The dock stretches 200 feet into the river with 3 berths for boats and seating for your enjoyment. Wildlife abounds; you may find yourself crabbing and fishing all day. Yes, our crabbing is excellent! The unique, secluded neighborhood consists of a single, mile-long road on its own peninsula with Dorchester's finest homes, stretching far into the Little Choptank River. The quiet street invites scenic bike rides or long walks to watch the sunsets. Mosquito Control measures provided for your comfort, The Area: A local country store, restaurant and boat ramp is 5 minutes away and the Chesapeake Bay, with its fishing, cruising, and endless sunsets, is out your window. The town of Cambridge is ten minutes away, with a pre-civil war, Victorian inspired downtown, and countless restaurants and shops. It’s not much further to visit the Maryland towns of Oxford, Easton, or Saint Michael's to walk the streets, take in the restaurants, or visit art shops and galleries.
On the property, relax! Go no further than the shoreline to find great swimming, crabbing, fishing, sunning, or boating. The sandy beaches are a luxury all year long, and the heated pool provides for a warm swim during those colder days and nights in May and September/October**. Endless porches and a stone fire pit is the centerpiece for many nighttime get-togethers. In the neighborhood, bike or walk down the neighborhood's 'private' peninsula and enjoy marvelous sunrises and sunsets among the finest of Maryland's summer and weekend retreats.
Sports both on water and land. Fishing Creek provides wide, almost endless passages for quiet kayaking, fishing, or pleasure boating. The waterskiing is excellent. The other side of the peninsula faces the Chesapeake Bay and Madison Bay and provides an open door to sailing or to the many top fishing spots. In town, there are boats to rent for a sail on the Choptank. Bike tours from all over the world flock to the eastern shore because it is flat, the roads are good quality, the traffic is light, and the sights are endless. Blackwater Refuge offers world-class nature views, and you can also bike in Easton, Saint Michaels, and Oxford, and there are many bike tour maps available to the visitor. There are two fantastic golf links nearby. The River Marsh course at the Hyatt Chesapeake is renowned. Hog Neck (18 miles) has a four-star rating from Golf Magazine. There are three additional courses between starting just nine miles away. "Hot Tub" as listed is a Jetted Jacuzzi tub in the Master bath. We have a steam shower as well!
* - Additional charge for groups larger than 14 ** - Pool heated *only* in May and between mid-September and closing for a fee ** - Pets: One (1) dog is permitted with a required pet fee and refundable pet deposit during any stay. All pet signs including hair waste etc. must be removed by the guest. ** - We've been renting our 5-Star property for 20 years and always share phone and email (required) to ensure we can be the very best host and so we can reach each other during your stay if needed! In addition, email allows us to send our welcome information which includes photos and links that can't be sent through the platform! ** - Outdoor (only) security cameras face the driveway and water
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Pets allowed: dogs less than 23 kg per pet (limit one pet total)
Must ask at booking. A fee plus deposit required.
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Smoking
Smoking is not permitted
We take this seriously, thanks
Signed rental agreement required. See full house rules thanks. Rates are set for 12 months. Ask about rates for stays that are longer than 12 months
Security: WiFi door lock for convenience for you & your guests. Exterior security cameras onsite; facing water and away from house
Pets: 1 dog, not allowed on furniture or off-leash. Fully-refundable peteposit req'd + $150 pet fee. Required to manage turnaround for the next guest
Important information
You need to know
Property # 219957
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: Only small, indoor parties
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Woolford
Located in Woolford, this holiday home is in the city centre and on the beach. The area's natural beauty can be seen at Blackwater National Wildlife Refuge and Bill Burton Fishing Pier State Park, while Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are cultural highlights. Travelling with kids? Consider Richardson Maritime Museum and Dorchester Arts Center. Jet skiing and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and horse riding nearby.
Blackwater National Wildlife Refuge - 7 min drive - 6.5 km
Harriet Tubman Underground Railroad National Historical Park - 18 min drive - 18.4 km
Long Wharf Park - 22 min drive - 23.6 km
Choptank River Lighthouse - 22 min drive - 23.6 km
Gerry Boyle Park at Great Marsh - 24 min drive - 24.6 km
Getting around
Cambridge Station - 22 min drive
Easton, MD (ESN-Easton - Newnam) - 46 min drive
Restaurants
Madison Bay - 8 min drive
The Neck District Grill - 36 min drive
Soft & Salty Seafood - 45 min drive
Willey's Seafood - 15 min drive
J-Bird's Church Creek Cafe - 12 min drive
Frequently asked questions
Does Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?
As of 20 Aug, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted on 10 Apr, 2027 start from S$5,683, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted pet-friendly?
Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.
How much is parking at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?
On-site parking is available at the property.
What time is check-in at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?
Check-in begins at 4:00 PM.
What time is check-out at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?
Checkout is at 10:30 AM.
Where is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted located?
Located in Woolford, this beachfront holiday home is in the city centre and within 9 mi (15 km) of Blackwater National Wildlife Refuge, Christ Rock Park and Harriet Tubman Underground Railroad National Historical Park. Snows Turn Park and Bettys Island are also within 12 miles (20 km).
About the host
Hosted by John
At first we rented out Saddle Beach a few weeks each summer to offset cost. Now we spend most of our time on the West Coast. Home is rented weekly in summer and weekends throughout the year. It's tough to be far away but we're still there often! Our full-time caretakers, Teri and Ken are wonderful and frankly, amazing. We also have a support group of great local vendors and contractors whose families have been the area for generations.
We love to help create vacation memories. Let us help you plan a great stay – enjy the property but you've got the potion to see the area as well. Go biking, hiking, sightseeing, crabbing, fish and boat around the area! Try the local restaurants and drive through the countryside – we have the areas only national wildlife refuge just 15 minutes away. Ask, ask ask! We want to help you plan! We have several repeat visitors each year. We are a real family and we have tremendous experience enabling family and similar vacations. We really do enjoy helping others make their own vacation memories on the Eastern Shore and the Chesapeake Region.
Why they chose this property
Size, beauty, location and amenities. Saddle Beach is the perfect vacation home for extended families and groups. It's gorgeous, with everything you need for best experience > on the property... or venture out to countless attractions, restaurants and recreation. Classic, private wraparound porches are a dream... The home was built with meticulous detail and an open floor plan, yet everyone says it feels warm and inviting. We built it for our family after a decade of planning.
The property is expansive and private and invites a week-long family event much like the family compounds of New England. It's a luxury property on the most elegant enclave of fine homes in the county, yet only ten minutes from the town of Cambridge, Maryland. The water is wide, calm and simply gorgeous! The Chesapeake Bay region is rural and water is everywhere.
What makes this property unique
You'll fall in love with the deep, stone wrap around porches, hand-cut, reclaimed walnut floors, and yet find it hard to stay inside with your own private pool, beach, dock, tidal pond and estate grounds.
Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests